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The ‘Preppy Killer’ and the Tabloid Sensation Still Defining 1980s New York Today

New York City was a different place in 1986 than it is today. There were a record 1,582 murders that year in the Big Apple, according to the NYPD, but the whole city was focused on taking the bite out of just one. 

During the morning hours of Aug. 26, 1986, detectives from the NYPD arrived to Central Park to find the grizzly scene of an 18-year-old woman with her clothing around her neck and cuts and bruises all over her body. Her skirt was raised above her waist, and her underwear lay 50 yards from the scene. 

Jennifer Levin, a soon-to-be-college student, had been killed. 

As detectives canvassed the scene, her killer, 20-year-old Robert Chambers, was lurking nearby, hiding as he watched the beginning of an investigation that would take hold of the city and country. 

A Fateful Meeting

Robert Chambers grew up in Manhattan with his Irish mother, who immigrated to the country before she had her son. She worked hard as a nurse to give him the very best. His father worked at MCA Records.

Chambers attended the best prep schools as a child, had the best clothes and was a regular during Sunday mass at his Catholic church where he was an alter boy. Chambers was even rumored to have had play dates with John F. Kennedy Jr. when they were both children

As much as his mother wanted the best for him, he only got as much of a privileged life as her paycheck allowed. Chambers was labeled as antisocial and had a hard time fitting in with his fellow classmates at dignified places of academia. 

Chambers attended Boston University but only completed one semester before leaving for academic reasons.  

In the summer of 1986, he met Jennifer Levin at his favorite watering hole, Dorrian’s Red Hand, on Manhattan’s Upper East Side. 

Levin grew up middle class in Long Island. She moved to Manhattan with her father before heading off to a Boston junior college.

New York was a hotbed of crime by the time the couple met. 

“Crime was rampant. I used to go to homicide scenes as an assistant district attorney, and I could go to three a night and I wouldn’t have to even report them to the press office because there was so many that they weren’t press worthy. Maybe that sets the tone for what it was like,” Chambers’ former attorney Roger Stavis told InsideEdition.com in 2018.

Wen Levin met Chambers at Dorrian’s in 1986, the two began their summer fling. She reportedly found his movie star good looks sexy. Things escalated on Aug. 26, in a way no one could have imagined. 

At 4:30 a.m., the couple left the bar and went to Central Park, where one life ended and another changed forever. Two hours after they left the bar, Levin’s lifeless body was found by a cyclist in the park. 

Following an investigation, Chambers was picked up by police and questioned. He had scratch marks on his face, which he claimed he got from his cat. He said he was raped by Levin. However, eventually his story changed and he explained that her death was an accident and that the couple had rough sex. 

Just about 24 hours after she was found dead, he was arraigned on a murder charge. 

“The Robert Chambers case came into the firm about a week after I started,” Stavis recalled. “He tried not telling the truth, and he ultimately did tell the truth. It then became the job of his defense attorneys to prove the truth of the final statement that he gave.”

Stavis was one of the first to visit Chambers in jail after he was arraigned. 

“He had scratch marks on his face, and when he was in police custody for a very long time, hours and hours and hours, that was a subject of the questioning by Detective Mike Sheehan, who was the lead detective in the case,” he recalled. 

Stavis said he was shocked that his client just stayed at the crime scene and hid as detectives arrived. 

“The first day I met him in recounting what happened, he said that he sat on the wall and watched the ambulances in the police and I was incredulous,” he said. “I was in shock. And so that’s why you sit there instead…if you’re not in shock, you’re going to get the hell out of there and you’re going to get on a train or a plane or an anything. To sit there, it reflects, and I always thought from day one, it reflected that this was not an intentional murder and this was a young man confronting bizarre circumstances and at a loss for how to act or what to do.”

Once the press got a hold of what Chambers looked like, he was dubbed “The Preppy Killer,” and the case became not just the talk of New York but of the country. 

The Trial of the Decade — and the Court of Public Opinion

Chambersfamily had secured bail through friends, the church and the owner of Dorrian’s. 

In the fall of 1987, the case went to trial, but not before a difficult jury selection. Because the story was everywhere and Chambers had become a tabloid sensation, it became hard to find jurors who hadn’t developed their own opinion of the “Preppy Killer.” 

“The first prospective juror was a young woman, and the judge … asked the young woman if she has any impressions … about Robert Chambers. She said, ‘He’s much better looking in person.’ She was excused,” Stavis recalled.

The defense tried to taint Levin by bringing her sexual activity into evidence and popularizing the “rough sex defense” term by claiming Levin tried to rape Chambers

Controversial prosecutor Linda Fairstein,who would go on to prosecute the “Central Park Five” case, said during the trial, “In more than 8,000 cases of reported assaults in the last 10 years, this is the first in which a male reported being sexually assaulted by a female.”

Assistant D.A. Steve Saracco also slammed the idea that Levin, who was about 110 pounds to Chambers’ 220-pound frame, could rape him. 

“I’ve been in this business for a while, and you’re the first man I’ve seen raped in Central Park,” he said. 

In April 1988, as the trial carried on, the case took a turn as the tabloid news show “A Current Affair” acquired footage of Chambers at a party joking about killing Levin.

In the home video, Chambers is seen playing with a Barbie doll and holding it to the camera. He says in a voice imitating a woman, “My name is… Oops! I think I killed it,” as he broke the head off the doll’s neck. In the video, he was also seen making choking and gagging gestures to four women dressed in lingerie

The video became a turning point for the case in the court of public opinion, but Chambers’ attorney felt it was much to do about nothing.

“My immediate reaction was it had nothing to do whatsoever with the death of Jennifer Levin. It had nothing to do with her death. It was him acting silly with a bunch of girls. … I watched it when it first came out and my reaction was, ‘Nothing to see here,’” he said. 

Just after the tape was making headline news outside of the courthouse, inside, Chambers took a plea deal after the jury was deadlocked. 

Chambers pleaded guilty to first degree manslaughter and was sentenced to five to 15 years in prison. 

A Quintessential New York Killing

Chambers served all 15 years of his sentence and was released in 2003. 

However, he wasn’t out of prison for too long. In 2008, he was arrested for selling drugs out of his New York City apartment. He was sentenced to 19 years in jail. His earliest release date is January 2024.

“It’s just pathetic. After all that, you just wasted your life,” Stavis said of his former client’s rearrest. 

Stavis said he has not kept in touch with his former client, saying, “I haven’t seen him for a long time. I did get letters and cards and things from him and I would exchange letters and cards, but that hasn’t been for quite some time.”

More than 30 years after Levin’s death and the crime that rattled the deadly decade of 1980s New York, the “Preppy Killer’s” story has been cemented in the history of the city.

“I guess it’s a story that encapsulates a lot of things that were going on in New York at the time. So you could say New York Mets win the World Series with Doc Gooden and Darryl Strawberry. Ed Koch, Robert Chambers. It’s just part of the zeitgeist, if you will, of the 1980s,” Stavis said. “Some of the corruption cases, the Parking Violations Bureau cases, Donald Trump. Whatever happened to him? But if you put it all together those are quintessential New York in the mid-1980s.”

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